This invention relates to 5-C-alkyl-3-O-arylmethyl and substituted arylmethyl-1,2-O-alkylidene-.alpha.-D-xylo-pentodialdofuranose, .alpha.-D-gludo- and .beta.-L-ido-pentofuranose derivatives and to the application of such compounds as herbicides and plant growth regulators. The invention also relates to the preparation of such compounds.
5-O-acetyl-1,2-isopropylidene-3-O-(4-methoxybenzyl)-6-deoxy-.alpha.-D-gluco furanose is described in Tetrahedran Letters, Vol. 23, No. 8, pp. 885-888 (1982) to illustrate the removal of O-p-methoxybenzyl protecting groups via DDQ oxidation.
The laboratory preparation of 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-.alpha.-D-xylo-heptofuranos-5- ulose and/or 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-.alpha.-D-xylohexofuranos-5-ulose for academic studies is described in Carbohydrate Research 31 (1973), pages 387-396; Carbohydrate Research 29 (1973), pages 311-323; Bulletin of the Chemical Society of Japan, 51 (12) (1978), pages 3595-3598; Journal of Organic Chemistry 44 (1979), pages 4294-4299; Journal of Organic Chemistry 46, (1981), pages 1296-1309; Journal of Organic Chemistry 27, 2107 (1962); Chem. Ber. 102, 820 (1969); Carbohydrate Research 26, 441 (1973); and Helv. Chem. Acta. 56, 1802 (1973).
U.S. Pat. Nos. 4,116,669, 4,146,384 and 4,330,320 and German Pat. No. DS 2,860,975 disclose a broad range of tetrahydrofuran derivatives and attribute herbicidal activity to these derivatives. U.S. Pat. Nos. 3,919,252, 4,004,991 and 4,207,088 disclose dioxalane derivatives and dioxane derivatives and attribute grass herbicidal activity to these derivatives. The sodium salt of 2,3:4,6-bis-O-(1-methylethylidene)-O-(L-xylo-2-hexulofuranosonic acid) is sold as a pinching agent for azaleas and ornamentals and a growth retardant for shrubs, hedges and ground covers and is disclosed in U.S. Pat. No. 4,007,206.
The application of 5-C-alkyl-3-O-benzyl-1,2-O-isopropylidene .alpha.-D-xylo-pentodialdofuranose as herbicides and plant growth regulators is described by B. McCaskey in commonly assigned copending application Ser. No. 387,590 filed June 11, 1982.
In my prior co-pending application Ser. No. 409,236, filed Aug. 18, 1982 now allowed U.S. Pat. No. 4,429,119, I disclosed certain 5-deoxy-3-O-arylmethyl or substituted arylmethyl-1,2-O-alkylidene-.alpha.-D-xylofuranose derivatives which are useful as herbicides and plant growth regulators. In my copending application Ser. No. 489,981, filed Apr. 29, 1983, I disclose certain 5-C-alkyl-3-O-arylmethyl or substituted arylmethyl-1,2-O-alkylidene-.alpha.-D-xylo-pentodialdofuranose and .alpha.-D-gluco-and .beta.-L-ido-pentofuranose derivatives which are also generally useful as herbicides.